Hong Kong has a unique postcolonial identity. After being colonised by Britain for over a century and a half, it was ceremoniously handed over to China in 1997, without necessitating any bloody wars or even skirmishes. Hong Kong has continued to enjoy a privileged status within China due to the doctrines enshrined in the ‘one country two systems’ policy. She has benefited from becoming part of a nation with the fastest growing economy in the world, and the people of Hong Kong have for the most part acquiesced to the reduction in levels of political freedom. However, recent events like the Umbrella Movement spearheaded mainly by student protesters has brought to the fore the cracks in Hong Kong’s postcolonial identity and the city finds itself once again precariously poised in a moment of transition. Theorising a connection between Hong Kong’s postcolonial predicament and the city state’s physical landscape, I analyse Hong Kong photographer Derrick Chang’s photos of Tin Shui Wai, a remote new town located on Hong Kong’s northwestern edge. Tin Shui Wai is a failed new town–it was developed to house workers who would serve the industries that were projected to develop there in the 1990s. However, these labour-intensive industries never materialised due to the meteoric rise of Guangdong’s manufacturing industry. Instead Tin Shui Wai has now come to be known as the ‘city of sadness’, notorious for its gruesome murders, high rate of domestic abuse and tragic suicides. Through an analysis of Chang’s photographs of Tin Shui Wai depicting isolation, stagnation and urban detritus, this article argues that the uncanny, spectral spaces of encounter raise questions and provide an alternative and more disquieting narrative of Hong Kong’s postcolonial identity. Copyright © 2017 International Visual Sociology Association.